The Perfect Cruising Sailboat Purchase Plan

Example of a Cruising Sailboat

The author's Aries 32 purchased using the same process on this hub.
The author's Aries 32 purchased using the same process on this hub. | Source

Research, Seach, Liquidate

You have the dream to purchase a cruising sailboat? To be a Brethren of the Coastand? To discover and plunder alongside the infamous Jack Sparrow? A dream to go by sail throughout the Caribbean and beyond?

You have the dream. So set to action and turn that inspiration into reality.


First, define your needs. Simply, what do you need this prospective sailboat to do? Second, define your cruising area. Where will this prospective sailboat go?

Answer the above questions then decide what type of sailboat meets your needs. Do you need a shoal draft sailboat with a center board, a modern sailboat with fin keel or the more classic appearance of a full keel double ended?

Internet forums and blogs provide a plethora of information that will help you to identify particular features on your prospective cruiser that you may want or can get along without. For example, do you need a hot water system or are you okay with walking from the marina facilities at the far end of the dock with a head of wet hair after a shower?

In addition to helping you figure out what you want in a sailboat the research may very well help you negotiate a better price.

Do you have the perfect cruising sailboat in mind? The perfect cruising sailboat is the one that works for you. This sailboat will please your eye, fullfil your immediate cruising needs, be right on target for your budget, and be near your current geographical area.

That last note is important. Do your best to find a sailboat near your current geographical area.

Transporting a boat overland is expensive and can add several thousands of dollars to the initial price of the boat. And sailing a boat that is bargain priced from somewhere over the rainbow to your local marina is not a wise choice. That is because some of the systems may be out of date and have the potential to cause serious and even life threatening problems.

Have patience and be diligent. Methodically check Craigslist and Ebay. As well as local marinas for auctions and sailboats listed for sale. Your cruising sailboat will show itself.


As you go about memorizing every sailboat on for what seems like a high school exam do not forget to get out and look and these sailboats in person.

Again, look to online forums to help you network with current sailors and cruisers. Of course you need to be serious. Most people who have been through the process of purchasing their own sailboat can quickly spot someone who is just kicking tires so to speak.

By the time you really start looking at sailboats in person you should have something in mind as far as size, rig options, and draft in mind. Just remember to be flexible too because a sailboat is a compromise of many many things.

  • What did I want?
  • I did race on a local circuit and most of the boats where more like cruisers than high-tech racers so I had plenty of experience on boats from 30 to 51 feet. Then I lived on a Catalina 27 for several years cruising the east coast of the United States. I meet other cruisers and learned more about what I wanted in my next boat.
  • As open of a floor plan as I could get, galley aft, a big v-birth, standing headroom, and a place where I could sit and write and not use that same space as the bed. After several years of searching I did find mostly what I wanted. The compromise came with the size of the cockpit. In reality I think it is too small but because of the other features that I wanted I decided to go with the boat and figure out how the cockpit will work into my use of the boat.


Once you have found the sailboat that matches your needs, you have been to the boat and inspected it yourself, and the sailboat is near your geographical area all that remains is to buy it.

You may want to get a surveyor to inspect the sailboat in addition to yourself.

If the sailboat is hauled out of the water inspection of the bottom will be easy. If the sailboat is in the water you will want to arrange a haul out to inspect the bottom.

  • I once put a deposit on a 35 foot sloop pending a haul out. I am glad I had the sailboat hauled. Once the boat was hauled out of the water there was a deformation around the keel to hull joint. The owner played it off as nothing important. I had a cautious feeling about that area. I asked the owner if I could remove the bottom paint and fairing compound around the area between the keel and the hull. He agreed.
  • The fiberglass was so weak that I was able to push my finger into the area and leave a good size dent. The research I had done prior to the haul out helped me to quickly determine the root cause of the situation as I had found documentation showing how the keel to hull joint was manufactured.
  • Could it be fixed, yes, but only through extensive repair.

Once the inspection is complete and you are satisfied and all your land living positions have been liquidated and you have been living in your bathroom for months to prepare for living on a sailboat then it is time buy the sailboat.

Do make sure you do have the cash in hand? If you don't have the cash in your hand stay home until you do. Or seriously rethink your cruising plans.

Do keep in mind the price for storage. And if you have a house or apartment ask yourself if you can you afford a rent payment plus a slip or storage payment?


Keep it simple.

Define your cruising needs and search for a local boat.

Research the local and on line sailing and cruising community for information.

Liquidate everything your own to make room for new boating toys.

Buy the sailboat and sail to the Caribbean.

The best time is now!

Sailboat Terminology

One World and Seven Seas

© 2014 Michael Thiel


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